Preparing graduate students for teaching careers in academia can involve myriad approaches. One such approach is facilitating authentic teaching opportunities for graduate students. The purpose of this multiple case study was to chronicle the perspectives of four humanities graduate students as they participated in a mentored teaching experience at a community college. Specific emphases included the evolution of participants' teacher identity and how a mentored teaching experience shaped participants' future career goals. Data sources consisted of semi-structured interviews, classroom observations, journal reflections, and classroom artifacts. Participants identified the fundamental importance of mentor faculty and diverse students as drivers in their own pedagogical development and reflected on the value of interpersonal connections in education. Implications include the need for more pedagogical transparency and discussion in humanities graduate education, as well as the potential of constructing cross-disciplinary and cross-institutional collaborations to support graduate students' professional development.